The synthesis of four UDP-GalNAc analogues (1-4) is described. The 3-, 4- and 6-deoxygenated analogues 1-3 were obtained by way of a divergent strategy starting from a 3,6-di-O-pivaloyl GlcNAc derivative as a common precursor. Analogue 4 bearing a N-trifluoroacetamido group was prepared from the trifluoromethylated oxazoline 24 as key intermediate. These compounds were designed to probe the substrate specificity of polypeptide-α-GalNAc transferases. © 2004 Published by Elsevier Ltd.
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